2-Chlorobenzenesulfonamide → HCID 178464645, compound

HRID 1484440Notes

Reaction equation

HRID 1484440 reaction equation
CS[C:3]([N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH3:13])=[N:8]1)=[N:4][CH2:5][CH3:6].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH2:24])(=[O:23])=[O:22]>C(#N)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:3]([NH:4][CH2:5][CH3:6])[N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH3:13])=[N:8]1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 814102-ChlorobenzenesulfonamideHCID 67360227HCID 67360227, compound

Product 1

HCID 178464645HCID 178464645, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.42 g (1 mol equiv.) 3,N-Diethyl-4,5-dihydro-pyrazole-1-carboximidothioic acid methyl ester and 1.43 g (1.05 mol equiv.) 2-chlorobenzenesulfonamide were added to 20 mL acetonitrile. The reaction mixture was refluxed overnight and volatiles were removed in vacuo. The residue was taken up in ethyl acetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue obtained after purification by flash chromatography on silica gel (Et2O) was triturated with diisopropyl ether to afford 2.08 g (81%) 2-chloro-N-[ethylamino-(3-ethyl-4,5-dihydro-pyrazol-1-yl)-methylene]-benzenesulfonamide. 1HNMR (400 MHz, CDCl3) δ 1.15 (t, J=7.3 Hz, 3H), 1.17 (t, J=7.3 Hz, 3H), 2.38 (q, J=7.3 Hz, 2H), 2.80 (t, J=9.8 Hz, 2H), 3.44-3.53 (m, 2H), 4.11 (t, J=9.8 Hz, 2H), 6.73 (br.s., 1H), 7.33 (dt, J=7.6, 2.0 Hz, 1H), 7.38 (dt, J=7.6, 2.0 Hz, 1H), 7.46 (dd, J=7.6, 2.0 Hz, 1H), 8.17 (dd, J=7.6, 2.0 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customvolatiles were removed in vacuo
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue obtained
  8. customafter purification by flash chromatography on silica gel (Et2O)
  9. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-65224fd36e3b4ce79d46f00785abb18c
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

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